5-乙氧基苯并呋喃-2-羧酸 | 206559-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 5-乙氧基苯并呋喃-2-羧酸
• 中文别名: 7-乙氧基苯呋喃-2-甲酸；7-乙氧基苯并呋喃-2-甲酸
• 英文名称: 7-(ethoxy)benzo[b]furane-2-carboxylic acid
• 英文别名: 7-ethoxybenzo[b]furan-2-carboxylic acid；7-ethoxybenzofuran-2-carboxylic acid；7-ethoxybenzo-furan-2-carboxylic acid；7-ethoxy-1-benzofuran-2-carboxylic acid
• CAS: 206559-61-7
• 化学式: C₁₁H₁₀O₄
• mdl: MFCD00060710
• 分子量: 206.198
• InChiKey: DQJVZIUEXPTEKX-UHFFFAOYSA-N

物化性质

• 熔点：
  195-199 °C
• 沸点：
  361.4±22.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 海关编码：
  2932999099
• 储存条件：
  保存方法：密封、阴凉、通风干燥处。

SDS

Name:	7-Ethoxybenzofuran-2-carboxylic acid Material Safety Data Sheet
Synonym:	None Known
CAS:	206559-61-7

Section 1 - Chemical Product MSDS Name:7-Ethoxybenzofuran-2-carboxylic acid Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
206559-61-7	7-Ethoxybenzofuran-2-carboxylic acid	98%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 206559-61-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 195 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C11H10O4
Molecular Weight: 206.20

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Acids, bases, oxidizing agents, reducing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 206559-61-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
7-Ethoxybenzofuran-2-carboxylic acid - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 206559-61-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 206559-61-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 206559-61-7 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-乙氧基苯并呋喃-2-羧酸 生成 (7-(Ethoxy)benzofuran-2-yl)-((S)-2-((pyrrolidin-1-yl)methyl)pyrrolidin-1-yl)methanone
  参考文献：
  名称：

  Amides of aminoalkyl-substituted azetidines, pyrrolidines, piperidines and azepanes

  摘要：

  氨基烷基取代的氮杂环戊烷、吡咯烷、哌啶和环庚烷的新型酰胺，以这些化合物作为药物组合物的用途，包含这些化合物的药物组合物，以及使用这些化合物和组合物进行治疗的方法。这些化合物显示出高度和选择性地结合到组胺H3受体，表明具有组胺H3受体拮抗、逆拮抗或激动活性。因此，这些化合物可用于治疗与组胺H3受体相关的疾病和疾病。

  公开号：

  US20030195190A1
• 作为产物：
  描述：

  3-乙氧基水杨醛 在 potassium carbonate 、 potassium iodide 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5-乙氧基苯并呋喃-2-羧酸
  参考文献：
  名称：

  作为针对秋水仙碱结合位点的微管蛋白聚合抑制剂的新型紫草素-苯并[b]呋喃衍生物的合成及生物学评价。

  摘要：

  设计并合成了一系列新的紫草素-苯并[b]呋喃衍生物作为微管蛋白聚合抑制剂，并对其生物学活性进行了评估。大多数化合物显示出与紫草素相当的抗癌细胞增殖活性，同时对非癌细胞具有较低的细胞毒性。其中，化合物6c对HT29细胞显示出强大的抗癌活性，IC50值为0.18μM，显着优于参考药物紫草素和CA-4。而且，6c可以抑制微管蛋白聚合，并与[3H]秋水仙碱竞争与微管蛋白的结合。进一步的生物学研究表明6c可以诱导细胞凋亡并使细胞线粒体去极化，调节HT29细胞中凋亡相关蛋白的表达。除了，6c激活了HT29细胞在G2 / M期的细胞周期停滞，并影响了细胞周期相关蛋白的表达。此外，6c显示出对细胞迁移和管形成的有效抑制，这有助于抗血管生成。这些结果促使我们将6c视为潜在的微管蛋白聚合抑制剂，值得进一步研究。

  DOI：

  10.1016/j.ejmech.2020.112105

文献信息

• Palladium-Catalyzed C−H Functionalization of Phenyl 2-Pyridylsulfonates
  作者：Bin Li、Dong-Dong Guo、Shi-Huan Guo、Gao-Fei Pan、Ya-Ru Gao、Yong-Qiang Wang

  DOI：10.1002/asia.201601413

  日期：2017.1.3

  An efficient palladium(II)‐catalyzed intermolecular direct ortho‐alkenylation and acetoxylation of phenols has been developed. The reaction proceeded via a seven‐membered cyclopalladated intermediate and showed complete regio‐ and diastereoselectivity. The approach also provided an efficient route for the synthesis of coumarins and benzofurans.

  已经开发出了一种有效的钯（II）催化酚间的分子间直接邻链烯基化和乙酰氧基化方法。反应通过一个七元的环钯中间体进行，显示出完全的区域选择性和非对映选择性。该方法还提供了合成香豆素和苯并呋喃的有效途径。
• 多巴胺D
  申请人：中国科学院分子细胞科学卓越创新中心

  公开号：CN111808056B

  公开（公告）日：2022-08-23

  本发明涉及一种多巴胺D2受体(DRD2)选择性激动剂及其在疾病治疗中的应用。具体的，本发明首次公开了一种对DRD2具有高度选择性的激动剂，其结构如式I所示，其可以作为一种药物来治疗以帕金森病为例的低多巴胺相关疾病，进一步的动物实验表明其可以用来治疗帕金森病，给帕金森病患者的治疗带来了新的希望，并以帕金森病为例证明其可以作为一种药物来治疗其他如注意缺陷多动障碍、垂体瘤、高催乳素血症、多动腿综合症、阴性精神分裂症等低多巴胺相关疾病。
• Discovery of (2<i>S</i>,3<i>R</i>)-<i>N</i>-[2-(Pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]oct-3-yl]benzo[<i>b</i>]furan-2-carboxamide (TC-5619), a Selective α7 Nicotinic Acetylcholine Receptor Agonist, for the Treatment of Cognitive Disorders
  作者：Anatoly A. Mazurov、David C. Kombo、Terry A. Hauser、Lan Miao、Gary Dull、John F. Genus、Nikolai B. Fedorov、Lisa Benson、Serguei Sidach、Yunde Xiao、Philip S. Hammond、John W. James、Craig H. Miller、Daniel Yohannes

  DOI：10.1021/jm301048a

  日期：2012.11.26

  (2S,3R)-N-[2-(Pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]oct-3-yl]benzo[b]-furan-2-carboxamide (7a, TC-561), a novel selective agonist Of the alpha 7 neuronal nicotinic acetylcholine receptor, has been as a promising drug candidate for the treatment of.cognitiVe. impairment 'associated with neurological.. disorders demonstrated more than a thousand fold separation between the affinities for the alpha 7 and alpha 4 beta 2 receptor subtypes and had no detectable effects On muscle or ganglionic nicotinic receptor subtypes, indicating a marked selectivity for the central nervous system over the peripheral nervous system. Results obtained from homology Modeling and docking explain the observed selectivity. 7a had positive effects cognitive, positive, negative symptoms of schizophrenia in animal models and was additive or synergistic with the antipsychotic. Clozapine. Compound 7a, as an augmentation: therapy to the standard treatment with antipsychotics, demonstrated encouraging results on measures. : of negative symptoms and cognitive dysfunction in schizophrenia and was well tolerated.: in a phase II clinical proof Of concept trial in patients With Schizophrenia.

  (2S,3R)-N-[2-(Pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]oct-3-yl]benzo[b]-furan-2-carboxamide（7a，TC-561）是一种新型选择性α7神经性烟碱型乙酰胆碱受体激动剂。它作为一种有前景的药物候选物，用于治疗与神经系统疾病相关的认知功能障碍。其对α7和α4β2受体亚型的亲和力分离系数超过千倍，并对肌肉或节交感神经烟碱型受体亚型无可检测到的影响，表明其对中枢神经系统相对于外周神经系统的显著选择性。 通过同源建模和对接研究获得的结果解释了观察到的选择性。在动物模型中，7a对认知功能、精神分裂症的阳性症状和阴性症状均表现出积极效果，并与抗精神病药物Clozapine表现出叠加或协同作用。在II期临床概念验证试验中，化合物7a作为标准抗精神病药物治疗的辅助疗法，在改善精神分裂症患者的阴性症状和认知功能障碍方面表现出令人鼓舞的结果，并且耐受性良好。
• Modulators of Protein Tyrosine Phosphatases (PTPases)
  申请人：——

  公开号：US20020151561A1

  公开（公告）日：2002-10-17

  The present invention provides novel thienopyridines, novel compositions, methods of their use, and methods of their manufacture, where such compounds of Formula 1 are pharmacologically useful inhibitors of Protein Tyrosine Phosphatases (PTPase's) including PTP1B, T cell PTP, 1 wherein X, R 1 , R 2 , R 3 , and R 4 are defined more fully in the description. The compounds are useful in the treatment of type 1 diabetes, type 2 diabetes, impaired glucose tolerance, insulin resistance, obesity, and other diseases.

  本发明提供了新型噻吩吡啶类化合物，新型组合物，其使用方法以及制备方法，其中Formula 1中的这些化合物在药理学上是蛋白酪氨酸磷酸酶（PTPase's）的有用抑制剂，包括PTP1B、T细胞PTP等，其中X、R1、R2、R3和R4在描述中有更详细的定义。这些化合物在治疗1型糖尿病、2型糖尿病、糖耐量受损、胰岛素抵抗、肥胖和其他疾病方面具有用处。
• Synthesis and cytotoxicity screening of derivatives of the simplified ecteinascidin pentacyclic skeleton as anticancer agents
  作者：Ju Guo、Yang Yang、Nan Wang、Zhanzhu Liu

  DOI：10.1016/j.tetlet.2018.07.027

  日期：2018.8

  A series of new ecteinascidin pentacyclic-derived compounds bearing aryl carboxylic amide side chains at C-22 have been designed and synthesized. The cytotoxicity evaluation confirmed their potent antitumor activity by use of eight different cell lines. Studies on the structure-activity relationship of them showed that the chemical structure of C-22 pendants have great effects on the tumor-killing

  设计并合成了一系列在C-22上带有芳基羧基酰胺侧链的新的十碳胞苷五环衍生物。细胞毒性评估通过使用八种不同的细胞系证实了其有效的抗肿瘤活性。对它们的构效关系的研究表明，C-22侧基的化学结构对杀肿瘤活性有很大的影响。值得注意的是，化合物6，7和8与苯并[ b ]噻吩-2-甲酰胺吊坠表现出优异的广谱的抗肿瘤活性与低IC 50个的10个值-7  M.